Graduation Present from a MILF

"I'm so sorry," Peter said as the girl turned around to face him.

"Peter Jameson?" she asked?

"Ashley? Ashley Britton? What are you doing here?"

Ashley Britton and Peter had been in school together since kindergarten. Peter had had a crush on her since then too. During their freshman year, before Ashley had ascended to the social heights of Kenway Academy and become captain of the cheer team, Peter had even dared to ask her out. She said no, of course. She hadn't been mean to him about it, but she also hadn't been nice. Every once in a while when they wanted to embarrass him, Peter's friends would bring up the fact that he'd been deluded enough to try to date the hottest girl in school. While Peter was far from the bottom of the school's social hierarchy he had also been quite far from the top. Very rarely did he get made fun of. But whenever he did, that incident always came up.

"Oh shit, Peter. Jack said you probably weren't going to come. I didn't realize you were here."

"Yeah, I came down last night."

"Oh well, cool, sorry about the drink," she said gesturing at his clothes. The two paused and glanced awkwardly at one another. Each clearly had something they wanted to say but weren't sure how to say it. Peter was about to begin when Ashley cut him off.

"By the way, do you know where your brother is? I've been here for almost half an hour and haven't seen him."

"Wait, wait wait," Peter said, furrowing his brow and trying to think through the din of the crowd. "How do you know my brother?"

Ashley shifted uncomfortably.

"You know. He and some of the other guys from the swim team come down and party with us at NYU every once in a while."

"Oh, I didn't know that."

"Yeah, so we've, uh, gotten to know each other. We hang out whenever he's in the city or wheneverI'm back up here."

"How often does he go down to New York?"

"Oh, idk, once a month? It's not a big deal. Just when we know of a fun house party or something."

Peter nodded while staring at the ground, trying to piece all of it together in his head. He was already resentful he had been sent on this task to hunt his brother down and this new information was not making it any easier.

"So have you seen him? Do you know where he is? I've texted him like 3 times but he hasn't responded," Ashley said, interrupting his thoughts once again.

Peter sighed and clenched his jaw.

"You know, I'm actually just trying to find him myself," he said, pushing past her and towards the house.

"Well, if you see him, tell him to text me back! I'm here for the whole weekend!"

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Peter opened the door to the house and breathed a sigh of relief. Unlike the rest of the house that was filled with party goers, this section was quiet. The dull echoes of music and chatter could be heard dimly through the thickly built and insulated walls, but the main noise in the hallway was just the low hum of the AC.

Glad for the reprieve, and no longer feeling much urgency to find his brother, Peter went to his own room to change into a dry shirt. After he did, he flopped on his bed and stared at the ceiling. All he could think about was Jack and Ashley. Peter had had a crush on Ashley for years. There was no girl that he'd masturbated to more than her. Just last week she'd posted an Instagram of herself in a new metallic silver bikini that had kept Peter going for days. But now, the only image in his head was his big, little brother, plowing his sexy, long-time crush. He could see her huge tits smushed up against Jack's chest, how she held onto his biceps and ripped forearms as he drove his smooth cock into her. He could hear her moan his name. Perhaps worst of all, Peter could feel himself getting hard just thinking about it. He wanted to see Ashley naked, to see her get fucked, even if he couldn't do it himself.

The buzzing of his phone interrupted his fantasy or nightmare or whatever the hell it was. It was his mom again.

"Yes mom?"

"Have you found him? We've been waiting for at least 10 minutes Peter!"

"No. I checked the pool and he wasn't there. Then I went and changed my shirt. It was still wet from when Jack hugged me earlier. Going to go check his room next and then I'll let you know."

"Ok hurry, your grandma and grandpa have to leave soon. I don't want to keep them waiting. It's a long drive back to their house and they're old."

Peter hung up and sighed again. Back to work. He lifted himself out of bed and then headed up the stairs towards Jack's loft, taking each step quietly and trying to listen for any signs of life in the room above him as he approached.

When he got to the door there was nothing but silence. Peter knocked.

"Jack, are you there? Mom's looking for you. Grandma and Grandpa have to leave and she wants you to come say goodbye."

More silence.

Peter frowned and knocked one more time.

"Jack?"

Nothing.

Peter tried the door. It was unlocked and he slowly opened it, peering in as he did so. Jack's messy, unmade bed was to the right, clothes filled the floor in the center of the room, and a desk with his laptop and a smattering of books and notepads sat on the left. Straight ahead were the large windows that overlooked the yard. The room was quiet and bright, but there was no Jack.

The dim hope that there might be a clue as to Jack's whereabouts inside coupled with a lurid curiosity about his brother's life prompted Peter to enter. He browsed around not finding much of anything. He peered through the window and saw a mostly empty yard plus the still chaotic pool. He kicked around some of Jack's dirty clothes but to no avail. On his bedside table he found a few empty beer bottles and a huge box of condoms. Pretty typical. Peter was already thinking about where else he could look for Jack and gave the room one last cursory glance before he left. And then he saw something.

Sitting on top of a pile of disorganized paper on Jack's desk was a gray envelope that had been torn open. A card that said "Congratulations Grad!" in bright red letters lay next to it. Peter glanced out the door and down the stairs behind him to make sure no one, especially not Jack, was coming up to the room, and then went over to the desk and picked up the card.

"Congratulations Jack! You know how proud I am of you and how much you've meant to me these past few months. Now that you're 18 and have officially graduated, I think it's time I gave you the gift we've been talking about. You deserve it. In the meantime, here's a little something to whet your appetite (I know photos are old fashioned, but I'm old fashioned and you'll just have to deal with it). Call me so we can set this up and don't make me wait. :) Love, Ali."

As Peter read through the card a handful of pictures fell out. He picked them up and flipped them over and almost immediately felt the blood start rushing to his dick. They were black and white pictures of Alice O'Connell in various stages of undress. The first two pictures were of Alice in a lace nightgown. One featured her bending over, smiling and beckoning with her finger towards the camera. Every inch of her tits, aside from her nipples, was visible as the camera's angle shot right down her cleavage. The second picture was of her lying down on her side, the nightgown riding up her leg. She was propping her head up with her hand and the wide smile of the first picture was replaced by her sultry lip-biting smirk. A third picture featured her sitting on a stool in a black g-string and black lace push-up bra. Her arms were pushing her hair back, her stomach was sucked in exposing the outline of abs, and her eyes stared into the distance. The final picture featured the same bra and g-string prominently strewn on the floor in the foreground, while Alice stood completely naked just behind them. Her legs were crossed, preventing any view of her pussy, while she wrapped her arms around her breasts, covering her nipples but not much else. Flipping the last picture over, Peter found what Jack must've found just a few minutes before him: Alice's phone number with a note that read "Come get me, tiger."

Peter's boner felt like it was about to explode out of his shorts. He didn't know what to do. His mind was racing. First Ashley, now Alice. His brother was the luckiest guy in the world. But Peter knew he couldn't daydream for long. His mom was still on his ass, and Jack was somewhere, presumably fucking Alice. They might even be on their way back here and since only one staircase led directly up to Jack's room, if he was caught here, there was no way out.

Thinking quickly, Peter whipped out his phone and snapped pictures of Alice's photos before he put them back in the card and placed the card back on Jack's pile of stuff. At least he had some new masturbation material, if nothing else.

Now, where could Jack have taken Alice? Peter walked to the windows and peered out over the backyard before it dawned on him. While the pool and all the seating areas around it were thronging with high school (and apparently college) party goers, the pool house at the end of the yard stood quiet and isolated. Pressing his face to the window, Peter squinted hard, hoping he might get confirmation of his theory or better yet, a glimpse of Alice, naked.

With a boner raging in his pants, and pictures of a nearly naked Alice on his phone, Peter almost involuntarily pulled his penis out of his shorts. He pulled up the picture of Alice with her bra and panties off and began stroking, imagining (not for the first time) that he was Jack putting his dick inside the milf of his dreams.

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"How long have you been dreaming of this, babe?"

"Oh my god, Jack, since January at least, when you came over for the first time and put together that new toy set for Ben. Do you remember?"

"I don't really remember the toy set, but I do remember not being able to keep my eyes off of you. Even after dealing with your kids all day, you were stunning Ali."

She smiled up at him, biting her lip as her fingertips traced their way down his pecs, weaved through every hard ridge of his abs, and finally rested on the elastic waistband of his light blue swimming trunks.

"How long have you been waiting for this, Jack?" Alice said from her knees, coyly tugging at the waistband without pulling his swimsuit off.

"Since the moment you moved in down the street from us 8 years ago."

"Did you ever dream you'd get this far with me?"

"I knew I would. It was just a matter of time."

Alice smiled and shook her head playfully.

"You naughty, naughty boy. Even when I was married, huh?"

"He was never good enough for you. That was obvious to anyone with half a brain."

A hush came over the room as Alice's hands both settled around the waistband and she began to pull it down. The nylon fabric moved slowly. Alice was taking her time, but the fabric was also caught on Jack's erect cock. Finally, with a little more effort, Alice yanked the swim trunks to the floor and Jack's dick popped out.

Like the rest of Jack's swimmer's body, his dick was shaved to complete smoothness. Its 8, veiny inches were capped off by a thick, dark purple, circumcised head. Jack smiled as Alice's jaw dropped to the floor.

"Oh Jack, this is bigger than I could've imagined..."

"Then you better get started."

At this, Alice's big blue eyes met Jack's with a fierce lust. She arched her back, pushing her tits (which for now were still in her dress) out towards Jack's crotch. Putting one hand on Jack's abs to brace herself, she used the other to guide his member to her mouth. As it got closer, she began by licking the tip. Bit by bit she took more until finally her light pink lips were wrapped around his whole head. Her eyes remained locked on his the entire time.

Each fraction of an inch Alice took into her mouth elicited more and more saliva. Her hand was constantly rubbing up and down the length of Jack's shaft, from his ball sack up to her lips and back down again, distributing her fluids over every inch of his dick. Her free hand mostly roamed Jack's chest, settling primarily on his abs. The more of his dick she took, the harder she squeezed his immovable, muscular core.

"Fuck yeah Ali. You know how to suck a dick, Jesus Christ."

Jack put one hand behind Alice's head, enjoying the feeling of her soft blonde hair. He stretched his other hand behind his own head, enjoying every second of this 40 year old milf blowing him in the pool house.

"Oh my god, you almost have it all, Ali. Not many girls have been able to do that. Can you take my whole cock?"

Alice's answer was only further soft slurping. But Jack could tell she was finally starting to struggle. She was about two incehs away from the base of his dick and he decided he should give her some help.

"Here baby, let me help you get all the way there."

Applying pressure to the back of her skull, Jack pushed Alice's head into his crotch while he slowly thrusted forward. Her slurping turned into a gag.

"That's what I like to hear. Just open up and take the whole thing," he said, thrusting a little faster and resolutely holding her head down.

Then she did something that surprised him. Her hand gripped his dick a bit harder and slowed down his thrusting until she controlled the speed. But at no point was she pulling his dick out of her mouth, she kept pushing it in, and in, and in, until finally his whole cock had disappeared down her throat.

"Holy shit, Ali."

Finally Alice released him, gagging up huge globs of saliva which she spit right back on his dick. She was out of breath and her eyes were watering, but her hand was rapidly stroking his cock, rubbing her saliva over every inch of his veiny member, while she looked up at him proudly.

"What do you think, baby?" she asked, still heaving and catching her breath.

"My balls are still pretty dry."

Without hesitating for a moment, Alice dropped lower and wrapped her lips around Jack's low hanging balls while her hand continued to stroke his shaft. She began by licking around them, tickling his scrotum with the tip of her tongue. And then she finally took one in her mouth, sucking it deep into her throat cavity like a high-pressured vacuum. Jack had never felt suction like that on his balls before.

"Holy shit, Ali, atta girl. Get the other one."

She immediately obliged, all the while beginning to stroke his dick even faster with her free hand

"That's it, babe." Jack intoned while Alice continued to suck softly on his testes. "Keep going."

Jack ran one of his hands through her hair, while he reached lower with his other hand and grabbed one of her breasts through the fabric of her dress.

"God I've waited years to see these. Take them out."

"You think we have enough time?" Alice asked, briefly coming up for air from beneath Jack's scrotum.

"I said take them out."

Alice smiled up at Jack. In public he was happy-go lucky and easy to be around. But in the bedroom his deep voice took on an authority and power she'd never seen before. She loved it. But she wouldn't make it that easy for him.

"I'm a little busy," she said, swallowing his cock again. This time she began to bob up and down rapidly, rubbing it with both hands as she did so. Her soft slurping turned into a rapid, deep gagging.

"Fuck, Ali." Jack groaned appreciatively

"You're so big, baby, I need both hands to take care of you." Alice said intermittently between tending to his cock. "I'll need your help if you want me to take my tits out."

Now it was Jack's turn to smile. Alice was a fucking minx.

"All you had to do was ask, Ali."

As she began bobbing up and down on his cock even faster than before, Jack bent over and fondled both of her breasts. After squeezing them hard, he reached up and peeled the straps of her dress off her shoulders and pushed them down onto her biceps. Alice obliged him and, pushing her mouth down as far on his cock as she could, she simultaneously slipped her arms out from under the straps of her dress,

Now with a clear approach, Jack shoved both hands down the top of her dress and under the lace of her bra, finally feeling the two mounds of flesh he had fantasized about for years. Her nipples pressed firmly into the palm of his hands. As he squeezed her tits with relish, Alice moaned. Jack lifted her breasts out of the bra and pulled them over her dress. For good measure, he yanked the front of the dress down a few inches so her tits hung out unencumbered.

"Holy shit, Ali, you have perfect tits. Like, the best tits I've ever seen."

He wasn't kidding. By Jack's reckoning she was a perfect 36c.The pair of tits was exactly symmetrical, twin spheres of soft flesh that were just as big in every direction. They protruded significantly on her hourglass figure. Granted, they weren't the perkiest tits Jack had ever seen--they hung just a bit when removed from her bra--but for a 40 year old woman that was a compliment, not a complaint. The pale, milky white flesh of her boobs were punctuated by bright pink nipples that stood at complete attention. Jack didn't think it was possible, but he felt himself get even harder in Alice's mouth.

Pulling Jack's now soaking wet dick out from between her lips, Alice began lightly slapping it between her exposed tits. She let some of the excess drool fall sloppily from her mouth. Some of it landed back on his cock, while some of it landed on her breasts.

"Oh, you like this don't you?" she cooed. "Do you want me to tittyfuck you?"

"Fuck yeah I do."

Alice let yet another gob of spit fall between her breasts. Taking one tit in each hand, she rubbed them together in the drool, and then wrapped them around Jack's rock hard cock. Without thinking, Jack began thrusting his dick up, as Alice moved her tits up and down around his shaft. Jack was so big that the tip of his penis almost reached Alice's open mouth with each thrust. Everytime Jack's purple head got close to her mouth, Alice bent her head over and tried to kiss the tip, dropping whatever excess spit she had on his shaft as she did so.

"God damn, I have dreamed about this for years Ali. Your tits are somehow even better than I imagined."

Jack grabbed the base of Alice's skull, both bracing himself and pulling her in closer to his dick. Then he began thrusting harder.

"Oh fuck yeah," he groaned in pleasure.

"Your dick feels so hard between my tits, baby. Can you fuck me harder?"

"Oh I can fuck you harder, Alice."

Jack stepped up even closer to Alice, eliminating all of the distance between them. He brusquely put his other hand behind her head. Using both hands, he forced her mouth down on his dick, while he began thrusting faster than he had all night.

"Is that what you want, you slutty housewife? You want me to facefuck you? Can you handle a real man's dick in your throat?"

Alice's only response was a deep gagging sound. She let go of her tits and grabbed Jack's thick legs for stability while Jack fired his cock rapidly in and out of her mouth, pushing in as far as possible each time.

"I bet limp dick Christopher never did this to you, did he? You could probably barely find his 3 inch cock underneath all that fat."

The sound of Jack's dick penetrating Alice's mouth and her subsequent gags were the only thing that filled the silence.

"How much more can you take? That's right. We're going until I say so," Jack said

He was grunting and out of breath from exertion. He'd never face fucked anyone this hard and this long before. But Alice just kept taking it. Finally, Jack felt the early stirring of the cum moving in his balls and pulled out. He had other things he wanted to do first. Meanwhile, Alice collapsed onto all fours, coughing up spit and trying to breathe.